The present invention relates to a mixture of compounds having the structures: ##STR2## wherein R.sub.1 and R.sub.2 are different and each represents ethyl or methyl and novel compositions containing such mixtures to augment, modify or enhance the flavor or aroma of foodstuffs or to impart flavor and/or aroma to foodstuffs and chewing gum and toothpastes and medicinal products.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) flavors and aromas to (or in) various consumable materials such as foodstuffs having chocolate and cocoa-like flavors. These substances are used to diminish the use of natural materials, some of which may be in short supply and to provide more uniform properties in the finished product.
Sweet, dark chocolate-like, cocoa powder-like aroma characteristics and dark chocolate-like, cocoa powder-like and spicey flavor characteristics with bitter chocolate after tastes are particularly desirable for many uses in foodstuff flavors, chewing gum flavors, toothpaste flavors and medicinal product flavors.
German Auslegschrift No. 2,402,416 discloses a sublimable perfumed composition in tablet form containing 1,3,5-triisopropyl-s-trioxane or 1,3,5-tri-t-butyl-s-trioxane as an active agent whereby the composition may be used to deodorize toilets, telephone mouthpieces, or give off insecticides.
2,4,6-Tri-s-butyl-1,3,5-trioxane is disclosed at Volume 19, page 391 of Beilstein; and it is further disclosed to be a "trimer" of methyl ethyl acetaldehyde (2-methyl butanal). An additional disclosure in Beilstein is at Volume 19, supplement 2 at page 403. Neither Beilstein reference discloses the organoleptic qualities of 2,4,6-triisobutyl-1,3,5-trioxane.
Indeed, the 1,3,5-triisopropyl-s-trioxane has little, if any, aroma or flavor to be of value in flavoring foodstuffs or tobaccos. It is, accordingly, quite surprising that the next adjacent methyl homologue, 2,4,6-triisobutyl-1,3,5-trioxane, has such intense aroma and flavor nuances as described herein.
Trialkyl substituted oxazolines are described in the prior art as being useful for modifying fish flavors in U.S. Pat. No. 3,627,540 issued on Dec. 14, 1971. More specifically, it is stated at Column 2, lines 12-27:
The seafood flavor characteristic of the pentadienal can further be varied by including one or more cyclic oxazo compounds, particularly .DELTA..sup.3 -oxazolines having the formula ##STR3## wherein R.sub.1, R.sub.2 and R.sub.3 are hydrogen, alkyl, or alkylene and can be the same or different. It is preferred in certain embodiments of the present invention to use lower alkyl derivatives of oxazoline, preferably those having up to about three carbon atoms in the alkyl group or groups. A preferred oxazoline in certain embodiments of the invention is 2,4,5-trimethyl-.DELTA..sup.3 -oxazoline. PA1 22. IDENTIFICATION AND FLAVOR PROPERTIES OF SOME 3-OXAZOLINES AND 3-THIAZOLINES ISOLATED FROM COOKED BEEF. Cynthia J. Mussinan, Richard A. Wilson, Ira Katz, Anne Sanderson, and Manfred H. Vock. International Flavors and Fragrances, Inc., 1515 Highway 36, Union Beach, New Jersey 07735. PA1 Four 3-oxazolines and two 3-thiazolines have been isolated from beef cooked in a sealed stainless steel vessel at 162.7.degree. and 182.degree.. The compounds were identified by matching retention times and mass spectra with those of authentic compounds synthesized in our laboratory. The compounds identified were 2,4-dimethyl-3-oxazoline; 2,4,5-trimethyl-3-oxazoline; 2,4-dimethyl-5-ethyl-3-oxazoline; 2,5-dimethyl-4-ethyl-3-oxazoline; 2,4-dimethyl-3-thiazoline; and 2,4,5-trimethyl-3-thiazoline. The synthesis, spectra and flavor properties of these and some related compounds will be discussed. PA1 R.sup.5 and R.sup.6 are each alkyl groups containing from 2 to 6 carbon atoms in an amount sufficient to enhance the flavor and aroma of said food base.
U.S. Pat. No. 3,627,540 does not imply, however, that the higher alkyl oxazoline analogue of the instant invention taken alone or in admixture with the 2,4,6-triisobutyl-1,3,5-trioxane of our invention, have flavor and aroma nuances of such quality and intensity as described herein.
Mussinan et al, "Identification and Flavor Properties of Some 3-Oxazolines and 3-Thiazolines Isolated from Cooked Beef," Abstracts of Papers, 170th Meeting, American Chemical Society, August 24-29, 1975, Port City Press, Baltimore, Md., Item No. AGFD 022, states:
None of the oxazoline compounds of Mussinan et al. have properties even remotely similar to those of the compounds containing the oxazoline moieties of the instant invention. Thus, the compounds containing the oxazoline moieties of the instant invention have unexpected, unobvious and advantageous properties with respect to their organoleptic characteristics when compared with the oxazolines of Mussinan et al. and U.S. Pat. No. 3,627,540.
In U.S. Pat. No. 3,892,879 (Division of Ser. No. 150,768 of June 7, 1971 which is U.S. Pat. No. 3,769,293 which in turn is a continuation-in-part of Ser. No. 34,876 filed May 5, 1970 (abandoned)) there is disclosed a method of flavoring a food base carrying a flavor selected from the group consisting of peanut, cocoa, chocolate, caramel, mint, butter, rum and fruit, said method comprising adding to said base a compound selected from the group consisting of those having the formulae: ##STR4## wherein: R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each alkyl groups containing up to 6 carbon atoms; and
Nothing in the prior art discloses the mixture of our invention.